Absolute chemical structure of the myxobacterial pheromone of Stigmatella aurantiaca that induces the formation of its fruiting body
1998; Oxford University Press; Volume: 165; Issue: 1 Linguagem: Inglês
10.1111/j.1574-6968.1998.tb13123.x
ISSN1574-6968
AutoresYuka Morikawa, Seiji Takayama, Ryosuke Fudo, Shigeru Yamanaka, Kenji Mori, Akira Isogai,
Tópico(s)Marine Sponges and Natural Products
ResumoStigmatella aurantiaca, a species of myxobacteria, produces a novel extracellular signaling molecule, 8-hydroxy-2,5,8-trimethyl-4-nonanone, which promotes its developmental cycle. To determine the absolute configuration of this pheromone, which contains one asymmetric carbon, we prepared the R- and S-enantiomers by stereoselective synthesis. The synthesized R- and S-enantiomers each showed nearly the same fruiting body-inducing activities as the natural pheromone. Gas chromatography-mass spectrometry (GC-MS) analysis using a chiral capillary column revealed that the naturally-produced pheromone is a mixture of both enantiomers.
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